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Search results; Over 1,000 homes in Old Saybrook

Guest favourite
Cottage in Old Saybrook
Luxury Driftwood Cottage @ Saybrook Point
3 bedrooms, 3 beds, 2 private bathrooms
7–13 Sept
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4.9 out of 5 average rating, 67 reviews
Top guest favourite
Home in Old Saybrook
The Saybrook Point Bungalow, Stroll to Downtown
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Cottage in Old Saybrook
The Cottage
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.75 out of 5 average rating, 254 reviews
Superhost
Home in Old Saybrook
Cozy beach side home Chalker Beach Old Saybrook
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Room in Deep River
Safari inspired little house
2 single beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Old Saybrook
Beachfront Home with Amazing Views | 5BR Sleeps 11
5 bedrooms, 7 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Cottage in Old Saybrook
Osprey Cozy Cottage | Near Downtown & Beaches
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Old Saybrook
Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
3 bedrooms, 6 beds, 1.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 101 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.91 out of 5 average rating, 139 reviews
Top guest favourite
Cottage in Old Saybrook
Beautiful View Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 165 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Old Lyme
Waterfront! The Perfect Cozy Cottage in Old Lyme
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Tiny home in East Lyme
Waterfront Bliss Tiny Home
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
13–18 Oct
4.94 out of 5 average rating, 172 reviews
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Home in Old Saybrook
Year Round Beach House in Old Saybrook, CT.- Pets
4 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 145 reviews
Home in Westbrook
Enjoy the Beach, Wine & Antique trails this FALL!
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Old Saybrook
Steps to Beach! *Cozy Cottage* Pet Friendly
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.92 out of 5 average rating, 104 reviews
Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.98 out of 5 average rating, 342 reviews
Top guest favourite
Flat in Westbrook
Meadowview & Pondside Retreat
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 50 reviews